F. Scott Fitzgerald famously wrote in his unfinished novel The Love of the Last Tycoon that “there are no second acts in American lives.” Not to disagree with a great American novelist, but life—be it sports, business, or even the cigar industry—is filled with examples of people being knocked down and picking themselves back up to return to their former conditions.

Returning to one’s former glory was the theme of the second session of Saturday’s Big Smoke seminar series, aptly named “Second Acts/Comebacks.”

The two panelists were in contrast on stage. Eiroa wore a sharply tailored, modern suit with a dress shirt and no tie, while Huber dressed in black t-shirt and jeans, his forearm sleeve tattoos visible to the crowd. The two may not share the same fashion sense, but they have one major thing in common: both men stepped away from the cigar industry for a spell after their former companies, where they earned much success, were bought out, only to return.

Eiroa used to be the president of Camacho Cigars, the family business once owned by his father, Julio, which was sold to the Oettinger Davidoff Group in 2008. After staying with the company for a few years, Eiroa left to start his CLE Cigar Co. in 2012. Huber, in turn, was the one-time marketing director at C.A.O. International Inc. before Scandinavian Tobacco Group, which owned C.A.O. at the time, merged assets with Swedish Match AB in 2010. Soon after that merger, C.A.O.’s headquarters in Tennessee were shuttered and moved to Virginia. Huber stayed behind.

Jon Huber, co-founder of Crowned Heads, describing what it's like to try to create a winning cigar brand for a second time.

Photos by David Becker/Getty Images

Christian Eiroa, the former president of Camacho, reinvented himself by creating CLE Cigar Co.

David Savona, senior editor of Cigar Aficionado, moderated the Second Acts seminar with Gordon Mott.

“The day after C.A.O. closed,” said Huber while on stage Saturday, “I had a meeting with the staff I have now, and we began brainstorming the philosophy for our next step.” When asked if there was ever any doubt of returning to the cigar business, Huber answered “I couldn’t imagine doing anything else.”

Eiroa shared Huber’s sentiment, adding that “he tried golf and fishing [before starting CLE], but sucked at both so he knew he had to get back into cigars.”

But how, exactly, does one return to the cigar industry? Both Eiroa and Huber agreed they didn’t want to come back and just do the same thing they were doing before, but saw it as an opportunity to challenge themselves and grow.

“I didn’t want to just create ‘C.A.O. 2.0,’” said Huber. “I thought of the whole thing as a music group. When musicians create a set list, they like to add variety. I didn’t want to roll out with ‘Crowned Heads this’ and ‘Crowned Heads that.”

The music theme was carried out in the second brand released by Crowned Heads, Headley Grange, which Huber explained was blended to taste like the opening drum beat from a Led Zeppelin song. (And all of the cigars made by Crowned Heads are made by Ernesto Perez-Carrillo, a former drummer and another cigar man enjoying his second act in business, having founded his own company after leaving his family’s La Gloria Cubana brand.)

Eiroa explained that he was determined to savor the second chance at making cigars.

“What would you do if you could do it all over again?” he asked from the stage. His goal when striking out anew with CLE, Eiroa explained, was to correct mistakes he made before, and to make cigars on a smaller, more personalized scale. “Every little thing is deliberate,” said Eiroa.

Both men said they intended to do things differently the second time around. “People expected Camacho,” said Eiroa, “but we didn’t want to do that.”

It was noted that Huber’s new cigars are very traditional in appearance, a departure from the avant-garde packaging he was part of during his days at C.A.O.

“That was part of my do-over,” Huber explained. “I felt like we go to a point with C.A.O. where a couple of projects went over the envelope, rather than just pushing it.”

Eiroa noted the change in the market from his early days in the business. He began making cigars in 1995, when a 52 ring was considered enormous. Now he sells a 7 by 70, a cigar he thought wasn’t going to work, “but it did.”

Both men commented on the quality of cigars on the present market, and how the entire market is more competitive. “There’s a lot of great product out there now,” said Huber.

Eiroa summed up the spirit of the day by giving a nod to the cigar lovers attending the seminar.